2-Aminothiophenol → ethyl (2E)-2H-1,4-benzothiazin-3(4H)-ylideneethanoate

HRID 1454219Notes

Reaction equation

HRID 1454219 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Cl[CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>CO>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1]/[C:11](=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])/[CH2:10]1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 5303657ethyl (2E)-2H-1,4-benzothiazin-3(4H)-ylideneethanoateYield 55.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

step 1—To a solution of 2-aminothiophenol (4.96 g, 39.6 mmol) in MeOH (200 mL) was added the ethyl 4-chloroacetoacetate (6.2 g, 38 mmol). After stirring at room temperature for 2 h the MeOH was removed under reduced pressure. The residue was dissolved in Et2O and washed with HCl (1N), saturated NaHCO3, and brine. The organic phase was dried over MgSO4, filtered and the solvent was removed under reduced pressure. The product was obtained from a minimum of EtOH to afford 5.0 g (54%) of 8: LCMS RT 3.7 min, M+H.

Workup

  1. customwas removed under reduced pressure
  2. dissolutionThe residue was dissolved in Et2O
  3. washwashed with HCl (1N), saturated NaHCO3, and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe product was obtained from a minimum of EtOH

Sources & evidence

ORD record
ord-4ef9a9011024411eb1e5ddf453a35913
Source dataset
uspto-grants-2009_01
Patent number
US07479489B2

Reaction notes

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